Ethyl 2-methylbut-2-enoate

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  • Identifiers

    CAS number
    55514-48-2

    Molecular formula
    C7H12O2

    SMILES
    CCOC(=O)C(=CC)C

    Safety labels

    Flammable
    Flammable

    Retention indicies (RI)

    • Carbowax: 1228.0

  • Odor profile

    Fruity 90.66%
    Sweet 69.63%
    Chamomile 57.18%
    Apple 56.44%
    Herbal 53.22%
    Green 52.77%
    Floral 50.85%
    Ethereal 49.01%
    Rummy 47.55%
    Winey 45.37%

    Scent© AI

  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    128.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    144°C

    Flash point est.
    40.43 ˚C

    Solubility expt.

    • Insoluble in water; soluble in oils
    • Soluble (in ethanol)

  • Synonyms

    • 55514-48-2
    • Ethyl 2-methylbut-2-enoate
    • Ethyl 2-methyl-2-butenoate
    • EINECS 259-688-8
    • DTXSID3047689
    • 2-Butenoic acid, 2-methyl-, ethyl ester
    • MFCD00015183
    • (E)-ethyl tiglate
    • ethyl-2-methyl-2-butenoate
    • DTXCID1027689
    • ethyl alpha,beta-dimethylacrylate
    • SY049480
    • DB-264932
    • NS00088395
    • 259-688-8

  • Applications

    Ethyl 2-methylbut-2-enoate (CAS 55514-48-2) is an alpha,beta-unsaturated ester with a characteristic fruity odor, used as a flavor and fragrance ingredient in foods, beverages, and confectionery (providing fresh, apple–pineapple–grape top notes) and as a perfumery material in fine fragrances, cosmetics, and personal care; in organic synthesis it serves as a convenient dienophile/Michael acceptor to build beta-substituted frameworks and heterocycles and as an intermediate toward pharmaceuticals and agrochemicals; it is also employed as a reference/aroma marker for GC/GC-MS calibration and quality control, and can be leveraged in specialty copolymer or resin/coating systems as a reactive aroma-bearing component.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1853.59
    methanol 1905.99
    isopropanol 1866.04
    water 10.47
    ethyl acetate 1584.75
    n-propanol 1710.49
    acetone 2294.02
    n-butanol 1504.41
    acetonitrile 3174.53
    DMF 2402.63
    toluene 986.01
    isobutanol 1396.6
    1,4-dioxane 2640.07
    methyl acetate 1856.43
    THF 2365.02
    2-butanone 2028.38
    n-pentanol 1333.41
    sec-butanol 1974.82
    n-hexane 607.81
    ethylene glycol 338.62
    NMP 2254.82
    cyclohexane 751.34
    DMSO 1823.84
    n-butyl acetate 1465.77
    n-octanol 1160.09
    chloroform 7510.34
    n-propyl acetate 1316.64
    acetic acid 1972.93
    dichloromethane 6910.54
    cyclohexanone 2504.72
    propylene glycol 534.75
    isopropyl acetate 908.97
    DMAc 1882.41
    2-ethoxyethanol 1407.12
    isopentanol 1249.18
    n-heptane 330.98
    ethyl formate 1445.69
    1,2-dichloroethane 3282.75
    n-hexanol 1195.1
    2-methoxyethanol 1672.73
    isobutyl acetate 703.86
    tetrachloromethane 1470.19
    n-pentyl acetate 1112.05
    transcutol 2399.84
    n-heptanol 818.46
    ethylbenzene 863.86
    MIBK 811.43
    2-propoxyethanol 1333.4
    tert-butanol 2176.9
    MTBE 1586.03
    2-butoxyethanol 999.26
    propionic acid 1617.85
    o-xylene 788.32
    formic acid 543.53
    diethyl ether 1662.89
    m-xylene 698.68
    p-xylene 1285.48
    chlorobenzene 1916.18
    dimethyl carbonate 527.16
    n-octane 220.85
    formamide 919.43
    cyclopentanone 2427.66
    2-pentanone 1444.94
    anisole 1306.49
    cyclopentyl methyl ether 1266.56
    gamma-butyrolactone 2795.98
    1-methoxy-2-propanol 1245.44
    pyridine 2735.67
    3-pentanone 1207.01
    furfural 2513.17
    n-dodecane 189.01
    diethylene glycol 796.8
    diisopropyl ether 552.99
    tert-amyl alcohol 2045.71
    acetylacetone 1319.59
    n-hexadecane 208.37
    acetophenone 1273.5
    methyl propionate 1197.65
    isopentyl acetate 1127.25
    trichloroethylene 6424.74
    n-nonanol 928.99
    cyclohexanol 1515.11
    benzyl alcohol 1093.77
    2-ethylhexanol 852.74
    isooctanol 676.01
    dipropyl ether 849.51
    1,2-dichlorobenzene 1787.06
    ethyl lactate 584.46
    propylene carbonate 1613.9
    n-methylformamide 1631.36
    2-pentanol 1257.08
    n-pentane 477.6
    1-propoxy-2-propanol 1006.59
    1-methoxy-2-propyl acetate 788.69
    2-(2-methoxypropoxy) propanol 806.49
    mesitylene 529.43
    ε-caprolactone 2037.54
    p-cymene 546.34
    epichlorohydrin 3058.6
    1,1,1-trichloroethane 3616.96
    2-aminoethanol 750.97
    morpholine-4-carbaldehyde 1982.21
    sulfolane 2707.09
    2,2,4-trimethylpentane 277.21
    2-methyltetrahydrofuran 2199.53
    n-hexyl acetate 1723.43
    isooctane 189.33
    2-(2-butoxyethoxy)ethanol 1098.64
    sec-butyl acetate 796.94
    tert-butyl acetate 945.5
    decalin 379.71
    glycerin 540.24
    diglyme 1964.53
    acrylic acid 1455.06
    isopropyl myristate 602.26
    n-butyric acid 1841.52
    acetyl acetate 952.03
    di(2-ethylhexyl) phthalate 479.96
    ethyl propionate 1124.21
    nitromethane 3126.21
    1,2-diethoxyethane 1258.65
    benzonitrile 2066.98
    trioctyl phosphate 409.61
    1-bromopropane 2248.27
    gamma-valerolactone 2567.62
    n-decanol 663.69
    triethyl phosphate 512.09
    4-methyl-2-pentanol 624.73
    propionitrile 2206.27
    vinylene carbonate 1824.04
    1,1,2-trichlorotrifluoroethane 1846.67
    DMS 901.3
    cumene 640.15
    2-octanol 831.34
    2-hexanone 1385.38
    octyl acetate 802.67
    limonene 730.42
    1,2-dimethoxyethane 2293.27
    ethyl orthosilicate 479.41
    tributyl phosphate 500.33
    diacetone alcohol 957.97
    N,N-dimethylaniline 953.59
    acrylonitrile 2756.37
    aniline 1155.41
    1,3-propanediol 1048.92
    bromobenzene 2175.2
    dibromomethane 4609.83
    1,1,2,2-tetrachloroethane 4500.4
    2-methyl-cyclohexyl acetate 783.73
    tetrabutyl urea 621.12
    diisobutyl methanol 463.17
    2-phenylethanol 967.95
    styrene 1139.42
    dioctyl adipate 747.72
    dimethyl sulfate 780.75
    ethyl butyrate 1116.87
    methyl lactate 560.68
    butyl lactate 764.18
    diethyl carbonate 841.55
    propanediol butyl ether 959.46
    triethyl orthoformate 689.12
    p-tert-butyltoluene 523.42
    methyl 4-tert-butylbenzoate 956.83
    morpholine 2667.88
    tert-butylamine 1689.57
    n-dodecanol 502.24
    dimethoxymethane 1168.37
    ethylene carbonate 1396.85
    cyrene 714.5
    2-ethoxyethyl acetate 1009.09
    2-ethylhexyl acetate 909.26
    1,2,4-trichlorobenzene 1931.48
    4-methylpyridine 2678.91
    dibutyl ether 1149.27
    2,6-dimethyl-4-heptanol 463.17
    DEF 1641.11
    dimethyl isosorbide 1127.61
    tetrachloroethylene 3049.07
    eugenol 923.35
    triacetin 1048.66
    span 80 803.7
    1,4-butanediol 625.16
    1,1-dichloroethane 4026.46
    2-methyl-1-pentanol 1216.47
    methyl formate 1268.14
    2-methyl-1-butanol 1321.56
    n-decane 303.34
    butyronitrile 2307.18
    3,7-dimethyl-1-octanol 860.17
    1-chlorooctane 915.59
    1-chlorotetradecane 374.35
    n-nonane 329.32
    undecane 230.39
    tert-butylcyclohexane 364.94
    cyclooctane 242.77
    cyclopentanol 1675.36
    tetrahydropyran 2449.21
    tert-amyl methyl ether 1205.98
    2,5,8-trioxanonane 1226.07
    1-hexene 1436.93
    2-isopropoxyethanol 981.97
    2,2,2-trifluoroethanol 608.86
    methyl butyrate 1620.71

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Roman chamomile (India) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.12%
Roman chamomile (Germany) 1a hydrodistillate 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.08%
Roman chamomile (Germany) 1b headspace 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.01%